Chlorodifluoromethane → 1-Bromo-4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 4-bromo-2-methoxy-3-(methoxymethoxy)phenol (700 mg, 2.66 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (734 mg, 5.32 mmol) cooled to −45° C. and chlorodifluoromethane (gas) was passed for 10 min and the resultant reaction mixture was heated to 80° C. for 2 h. The reaction mixture was quenched with ice-cold water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were dried over anhy. sodium sulphate and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 0-5% ethyl acetate in pet ether) afforded 1-Bromo-4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)benzene as a liquid (250 mg, 30%).

Provenance & Evidence